scholarly journals Total Synthesis of (±)-Lysergic Acid, Lysergol, and Isolysergol by Palladium-Catalyzed Domino Cyclization of Amino Allenes Bearing a Bromoindolyl Group

2011 ◽  
Vol 13 (8) ◽  
pp. 2145-2145 ◽  
Author(s):  
Shinsuke Inuki ◽  
Shinya Oishi ◽  
Nobutaka Fujii ◽  
Hiroaki Ohno
Keyword(s):  
Total Synthesis ◽  
Lysergic Acid ◽  
Palladium Catalyzed

scholarly journals Total Synthesis of (±)-Lysergic Acid, Lysergol, and Isolysergol by Palladium-Catalyzed Domino Cyclization of Amino Allenes Bearing a Bromoindolyl Group

2008 ◽  
Vol 10 (22) ◽  
pp. 5239-5242 ◽  
Author(s):  
Shinsuke Inuki ◽  
Shinya Oishi ◽  
Nobutaka Fujii ◽  
Hiroaki Ohno
Keyword(s):  
Total Synthesis ◽  
Lysergic Acid ◽  
Palladium Catalyzed

scholarly journals Correction to Total Synthesis of Lysergic Acid

2014 ◽  
Vol 16 (4) ◽  
pp. 1269-1269 ◽  
Author(s):  
Satoshi Umezaki ◽  
Satoshi Yokoshima ◽  
Tohru Fukuyama
Keyword(s):  
Total Synthesis ◽  
Lysergic Acid

scholarly journals Total Synthesis of (+)-Spiroindimicin A via Asymmetric Palladium-Catalyzed Spirocyclization

2021 ◽  
Author(s):  
Zhen Zhang ◽  
Sneha Ray ◽  
Leah Imlay ◽  
Lauren Callaghan ◽  
Hanspeter Niederstrasser ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Human Health ◽  
Neglected Tropical Diseases ◽  
Indole Alkaloids ◽  
Sleeping Sickness ◽  
Tropical Diseases ◽  
African Sleeping Sickness ◽  
Palladium Catalyzed ◽  
Natural Precursor

<p>The spiroindimicins are a unique class of chlorinated indole alkaloids characterized by three heteroaromatic rings structured around a congested spirocyclic stereocenter. Here, we report the first total synthesis of (+)-spiroindimicin A, which bears a challenging C-3’/C-5’’-linked spiroindolenine. We detail our initial efforts to effect a biomimetic oxidative spirocyclization from its proposed natural precursor, lynamicin D, and describe how these studies shaped our final abiotic 9-step solution to this complex alkaloid built around a key asymmetric Pd-catalyzed spirocyclization. Scalable access to spiroindimicins A, H, and their congeners has enabled discovery of their activity against several parasites relevant to human health, providing potential starting points for new therapeutics for the neglected tropical diseases leishmaniasis and African sleeping sickness.</p>

Sign in / Sign up

Export Citation Format

Share Document